Brønsted Acid Catalyzed Homoconjugate Addition of Organotrifluoroborates to Arylated Cyclopropyl Ketones

Org Lett. 2016 Aug 5;18(15):3786-9. doi: 10.1021/acs.orglett.6b01795. Epub 2016 Jul 13.

Abstract

A novel and practical homoconjugate addition of alkenyl, alkynyl, heteroaryl, and aryl trifluoroborates to arylated cyclopropyl ketones to synthesize γ,γ-disubstituted ketones is reported. A preliminary mechanistic proposal involving ketone protonation, an intermediary carbocation, and intermolecular nucleophile addition has been made based on control studies.

Publication types

  • Research Support, Non-U.S. Gov't